US10069081B2ActiveUtilityA1
Organic electroluminescent materials and devices
Est. expiryDec 7, 2032(~6.4 yrs left)· nominal 20-yr term from priority
C07D 409/14C09K 2211/1044C09K 2211/1092C07D 403/14C07D 403/10C09K 2211/1029C09K 2211/1059C07D 495/04C07D 405/14C09K 2211/1011C07D 493/04C09K 2211/1088C09K 2211/1007C09K 2211/1014C07D 491/048C09K 11/06H01L 51/5012H01L 51/006H01L 51/0067H01L 51/0061H01L 51/0074H01L 51/0054H01L 2251/5376H01L 51/0072H01L 51/0073H10K 85/6576H10K 85/6574H10K 85/654H10K 85/622H10K 50/11H10K 2101/27H10K 85/6572H10K 85/633H10K 85/636
80
PatentIndex Score
1
Cited by
181
References
19
Claims
Abstract
Devices containing novel carbazole-containing compounds are provided. The novel compounds also contain electron donor groups, aryl linkers, and at least one nitrogen heterocycle. These novel organic compounds can exhibit delayed fluorescence in the devices.
Claims
exact text as granted — not AI-modifiedThe invention claimed is:
1. A first device comprising a first organic light emitting device, comprising:
an anode;
a cathode; and
an emissive layer, disposed between the anode and the cathode;
wherein the emissive layer comprises a compound having the formula:
wherein Z 1 , Z 2 , Z 3 , Z 4 and Z 5 are each independently selected from group consisting of CR 9 and N;
wherein any adjacent R 9 are optionally joined to form a fused ring;
wherein at least one of Z 1 , Z 2 , Z 3 , Z 4 and Z 5 is N;
wherein L 1 is selected from the group consisting of:
and combinations thereof;
wherein X 1 is O, S, or CRR′;
wherein R, R′ are optionally joined to form a ring;
wherein n 1 is an integer from 1 to 20;
wherein L 1 can be further substituted by a substituent selected from the group consisting of alkyl, aryl, and heteroaryl;
wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 comprises at least one electron donor group selected from the group consisting of:
wherein X and Y is selected from the group consisting of O, S, NR 14 ; and
wherein R 11 , R 12 , R 13 and R 14 are selected from the group consisting of aryl and heteroaryl;
wherein any two adjacent R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are not joined to form a ring;
wherein m is an integer from 1 to 20;
wherein n 2 is an integer from 1 to 20;
wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 do not contain an electron acceptor group;
wherein R 9 does not contain an electron donor group;
wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combinations thereof;
wherein R 9 , R, and R′ are independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, heteroalkyl, arylalkyl, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combinations thereof; and
wherein at least one of Z 1 , Z 2 , Z 3 , Z 4 and Z 5 is CR 9 wherein R 9 is selected from aryl and heteroaryl, and can be further substituted.
2. The first device of claim 1 , wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 comprises the electron donor group selected from the group consisting of:
3. The first device of claim 1 , wherein the compound has the formula:
and
wherein R 91 and R 92 are independently selected from aryl or heteroaryl, and can be further substituted.
4. The first device of claim 1 , wherein the electron donor group is selected from the group consisting of:
5. The first device of claim 1 , wherein the compound is selected from the group consisting of:
6. The first device of claim 1 , wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 comprises at least one electron donor group having the structure
7. The first device of claim 1 , wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 comprises at least one electron donor group having the structure
8. The first device of claim 1 , wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 comprises at least one electron donor group having the structure
9. The first device of claim 1 , wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 comprises at least one electron donor group having the structure
10. The first device of claim 1 , wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 comprises at least one electron donor group having the structure
11. The first device of claim 1 , wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 comprises at least one electron donor group having the structure
12. The first device of claim 1 , wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 comprises at least one electron donor group having the structure
13. The first device of claim 1 , wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 comprises at least one electron donor group having the structure
14. The first device of claim 1 , wherein L 1 is
15. The first device of claim 1 , wherein L 1 is
16. The first device of claim 1 , wherein L 1 is
17. The first device of claim 1 , wherein L 1 is
18. The first device of claim 1 , wherein L 1 is
19. The first device of claim 1 , wherein the first device is a consumer product selected from the group consisting of flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads up displays, fully transparent displays, flexible displays, laser printers, telephones, cell phones, personal digital assistants (PDAs), laptop computers, digital cameras, camcorders, viewfinders, micro-displays, vehicles, a large area wall, theater or stadium screen, and a sign.Cited by (0)
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